4 Sad Songs From 1969 That Perfectly Captured the End of an Era

The year 1969 marked the end of one of the most incredible musical eras of the 20th century. And with it, there was a sense of mourning in the music that dropped that year. The Vietnam War was raging on, things were changing and stagnant all at once, and plenty of sad songs released in 1969 reflected the way most people felt at the time. Let’s take a look at a few examples.

“He Ain’t Heavy, He’s My Brother” by The Hollies from ‘He Ain’t Heavy, He’s My Brother’

This very emotional ballad from The Hollies is all about carrying another person’s burdens throughout one’s own life. The Hollies turned this heartbreaker into a hit, but it was actually originally released by Kelly Gordon that same year. The Hollies’ version was a Top 10 hit globally, peaking at No. 7 on the Billboard Hot 100 chart.

“The Boxer” by Simon & Garfunkel from ‘Bridge Over Troubled Water’

“The Boxer” could easily be one of the saddest songs that Paul Simon ever wrote. This folk-rock ballad is a lament of sorts about the life of a boxer who suffers from loneliness and poverty. Though, between the lines, one can see how this song could be autobiographical and largely inspired by Biblical stories. “The Boxer” peaked at No. 7 on the Hot 100 chart and did similarly well in the UK.

“Leaving On A Jet Plane” by John Denver from ‘Rhymes & Reasons’

One could listen to this folk song and hear it as a bittersweet, poignant “farewell” song to the 1960s, as well as John Denver’s personal farewell to anything: leaving one’s hometown, going on tour, embarking on some sort of adventure with no return ticket. I personally love Denver’s version, but it’s worth noting that the group Peter, Paul And Mary released a more politically-charged version of the song later that year that became a hit, peaking at No. 1 on the Hot 100. One could hear their version as a song sung from the perspective of a soldier about to be deployed.

“And When I Die” by Blood, Sweat & Tears from ‘Blood, Sweat & Tears’

Nobody wants to grapple with their own mortality. But this Blood, Sweat & Tears song did exactly that in a particularly reflective and beautiful way. There were plenty of sad songs like it in 1969, but “And When I Die” boasts a particularly positive outlook on one’s impending doom. We all die someday, after all. This song resonated with listeners at the time, enough to peak at No. 2 on the Hot 100 chart.

(Photo by Chris Walter/WireImage)